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T90301

Sigma-Aldrich

3-(2-Hydroxyethyl)indole

97%

Synonym(s):

2-(3-Indolyl)ethanol, 3-Indoleethanol, IEA, NSC 3884, Tryptophol

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About This Item

Empirical Formula (Hill Notation):
C10H11NO
CAS Number:
526-55-6
Molecular Weight:
161.20
Beilstein/REAXYS Number:
125553
EC Number:
208-393-2
MDL number:
MFCD00005659
UNSPSC Code:
12352100
PubChem Substance ID:
24900580
NACRES:
NA.22

Quality Level

100

assay

97%

mp

56-59 °C (lit.)

SMILES string

OCCc1c[nH]c2ccccc12

InChI

1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

InChI key

MBBOMCVGYCRMEA-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activities
  • Anti-HIV-1 agents
  • Inhibitors of Protein-Protein Interactions
  • Partial agonists of the serotonin 5-HT1A receptor
  • Growth hormone secretagogues
  • Vascular endothelial growth factor (VEGF) inhibitors
  • A2B adenosine receptor ligands
  • Potential detoxification inhibitors of the crucifer phytoalexin brassinin
  • Inhibitors of interleukine 6
  • Dual binding site acetylcholinesterase inhibitors

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ivan Kosalec et al.
Arhiv za higijenu rada i toksikologiju, 62(1), 41-49 (2011-03-23)
Tryptophol is an aromatic alcohol and secondary metabolite of the opportunistic fungus Candida albicans. Although its toxicity profile at cell level has been poorly investigated, recent data point to cytotoxic, cytostatic, and genotoxic effects in lymphocytes and the induction of
Chuan Liu et al.
Organic letters, 14(17), 4525-4527 (2012-08-16)
Copper(I)-catalyzed dearomative arylation and vinylation of 2-substituted tryptophols were realized with a subsequent cyclization reaction. The cascade dearomatization sequence provided versatile furoindoline derivatives with two quaternary carbon centers in good to excellent yields.
Atiqur Rahman et al.
Bioscience, biotechnology, and biochemistry, 74(11), 2202-2208 (2010-11-13)
Rhizobacteria isolated from wild dipterocarp saplings in Central Kalimantan, Indonesia, were subjected to Salkowski's reagent test, which is often used in detecting indolic substances. Among 69 isolates grown in a low-nitrogen medium supplemented with L-tryptophan (TRP), culture fluids of 29
Hexon Angel Contreras-Cornejo et al.
Plant physiology, 149(3), 1579-1592 (2009-01-30)
Trichoderma species belong to a class of free-living fungi beneficial to plants that are common in the rhizosphere. We investigated the role of auxin in regulating the growth and development of Arabidopsis (Arabidopsis thaliana) seedlings in response to inoculation with
Alessandro Palmieri et al.
Organic & biomolecular chemistry, 10(17), 3486-3493 (2012-03-22)
Reduction of ketosulfonyl indoles with sodium borohydride provides a ready entry to tryptophols in a regiocomplementary fashion with respect to the traditional oxirane ring-opening by indoles under Friedel-Crafts conditions. Compared to traditional β-ketosulfones, ketosulfonyl indoles show a peculiar behavior since
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